The Sack of Wexford took place in October 1649, during the Cromwellian conquest of Ireland, when the New Model Army under Oliver Cromwell took Wexford town in south-eastern Ireland. The English Parliamentarian troops broke into the town while the commander of the garrison, David Sinnot, was trying to negotiate a surrender – massacring soldiers and civilians alike. Much of the town was burned and its harbour was destroyed. Along with the Siege of Drogheda, the sack of Wexford is still remembered in Ireland as an infamous atrocity.

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Wexford was held by Irish Catholic forces throughout the Irish Confederate Wars. In the Irish Rebellion of 1641, over 1500 local men mustered in the town for the rebels. In 1642, Lord Mountgarret, the local Commander of the Confederate Catholic regime, ordered Protestants to leave Wexford. About 80 English Protestant refugees drowned when the boat evacuating them from Wexford sank.

Wexford was also the base for a fleet of Confederate privateers, who raided English Parliamentary shipping and contributed 10% of their plunder to the Confederate government based in Kilkenny. By 1649, there were over 40 such vessels operating from the town, many of them originating in Dunkirk, but attracted to Wexford by the prospect of plunder. English Parliamentary sources reported that the privateers' raids were severely disrupting shipping between Dublin, Liverpool and Chester. The Confederate privateers fought a "dirty war" with English Parliamentarian naval forces. In 1642, Parliamentary ships began throwing captured Wexford sailors overboard with their hands tied. In reprisal, 150–170 English prisoners were kept in Wexford and threatened with death if such killing continued.

In 1648, the Confederates and Royalists in Ireland signed a treaty joining forces against the English Parliament. After Cromwell's landing in Ireland in August 1649, therefore, Wexford was a key target for the Parliamentarians, being an important port for the Royalist alliance and a base for the privateers.

Cromwell arrived at Wexford on 2 October 1649 with about 6000 men, eight heavy siege guns and two mortars. On 6 October, Cromwell concentrated his force on the heights overlooking the southern end of the town.

The town's garrison initially consisted of 1500 Confederate soldiers under David Sinnot. However, the morale of the town was low – perhaps as a result of hearing the fall of Drogheda on 11 September – and many of the civilians in Wexford wanted to surrender. Sinnot however, appears to have strung out surrender negotiations with Cromwell and was steadily reinforced, bringing his garrison strength up to 4,800 men by 11 October. In addition, the main Royalist/Confederate force under James Butler, 1st Duke of Ormonde was close by at New Ross.

Sinnot insisted on several conditions for surrender that Cromwell would not countenance, including the free practice of the Catholic religion, the evacuation of the garrison with their arms and the free passage of the privateer fleet to a friendly port.

Negotiations were re-opened when Cromwell's guns blasted two breaches in the walls of Wexford castle, opening the prospect of an assault on the town. However, while negotiations were still ongoing, the town was unexpectedly stormed and sacked on 11 October 1649. The circumstances are confused and contentious. It does not appear that Cromwell ordered an assault on the town, much less its sacking.

Cromwell's final letter to Sinnott on 11 October 1649 read as follows – it unequivocally expresses willingness to give terms:

Sir, I have had the patience to peruse your propositions; to which I might have returned an answer with some disdain. But to be short I shall give the soldiers and non-commissioned officers quarter for life and leave to go to their several habitations......and as for the inhabitants, I shall engage myself that no violence shall be offered to their goods, and that I shall protect their town from plunder.

While negotiations were still proceeding, however, Stafford, the English Royalist captain of Wexford Castle (part of the town's defences), surrendered the castle, for reasons that have never been determined. The troops of the New Model Army, on their own initiative, immediately assaulted the walls of the town, causing the Confederate troops to flee in panic from their positions. The Parliamentarians pursued them into the streets of Wexford, killing many of the town's defenders. Several hundred, including David Sinnot, the town governor, were shot or drowned as they tried to cross the river Slaney. Estimates of the death toll vary. Cromwell himself thought that over 2000 of the town's defenders had been killed compared with only 20 of his troops. Several Catholic priests, including seven Franciscans were killed by the Roundheads. Much of the town, including its harbour, was burned and looted. As many as 1,500 civilians were also killed in the sacking. This figure is difficult to corroborate but most historians accept that many civilians were killed in the chaos surrounding the fall of Wexford.

The destruction of Wexford was so severe that it could not be used either as a port or as winter quarters for the Parliamentarian forces. One Parliamentarian source therefore described the sack as "incommodious to ourselves". Cromwell reported that the remaining civilians had "run off" and asked for soldiers to be sent from England to re-populate the town and re-open its port.

In relation to Wexford, as with his Siege of Drogheda, the contention that Cromwell massacred civilians is disputed. Cromwell did not mention civilian casualties in his report on the siege. However, a request for compensation from the town of Wexford to the restored monarchy in the 1660s stated that 1,500 townspeople lost their lives in the sack. James Scott Wheeler, author of "Cromwell in Ireland" judges that, "unquestionably, hundreds of non-combatants were killed by the rampaging soldiers". Even Tom Reilly, author of "Cromwell an Honourable Enemy" (which gives a favourable account of Cromwell's conduct in Ireland) concedes, "there are many more references to the deaths of women and children at Wexford than at Drogheda and this fact is difficult to ignore".

Reilly's main defence of Oliver Cromwell at Wexford is that the sack of the town was not his intention and that he bears no responsibility for it. While Cromwell did not order the assault on the town, he made no attempt to stop it or to punish the perpetrators. Indeed he justified the conduct of his troops, saying of Wexford that, "they were made with their blood to answer for the cruelties they had exercised upon diverse poor Protestants". This referred to the treatment of Protestants in the town after 1641 and to the activities of the privateers.